


The Ride

by CraftKookies



Category: On My Block (TV)
Genre: M/M
Language: English
Status: Completed
Published: 2019-04-23
Updated: 2019-04-23
Packaged: 2020-01-24 08:19:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,251
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18567487
Author URL: https://archiveofourown.org/users/CraftKookies/pseuds/CraftKookies
Summary: Oscar just got out of jail for the second time and for some reason Ruby is the one who picks him up.





	The Ride

Well once again his boys had gotten sloppy and caught by the cops and just like he had before Cesar had gotten to middle school he took the fall for his boys.

If had been one of his veterans Oscar would have let them go in for themselves, but these fools were brand new. Their bruises from being jumped in hadn’t even fully healed. They were too cocky and reckless with a job they didn’t get approval for.

So back in he went.

Oscar could handle jail, same way he could handle the life...that didn’t mean he liked it, any of it.

He hated the life if he were to be honest with himself; he didn’t like the violence, even though he was good at it. The constant risk of him or Cesar getting caught by the police or Profit$ kept him on edge, so he smoked and drank to keep himself sedated most of the time. He had an entire hood to look over and it took away from his time with his brother.

If Oscar had it his way he would own a little restaurant, nothing five star but it would be his, he’d have Cesar and his friends help out after school. Even that annoying tiny one.

Ruby.

The one he had actually been talking about when he was high off his ass with his little brother, once he’d finally came down he understood why his brother thought he was talking about Monse.

“That little friend of yours homes...the one with the nice ass. I been looking...waiting. Trying to wait until the ass is legal, but damn it’s getting harder to keep my hands off it.”

All that mess was over two years ago.

Now his baby brother was a senior with grades good enough to get a scholarship to UCLA, if he kept his grades high enough and got his shit straight with financial aid then he could get a full ride.

And he was happy that his coming home party is also going to double as a celebration for Cesar’s college acceptance.

He had been given his personal belongings and was being walked out to freedom.

‘You’re one of the lucky ones Santo, you got a car waiting for you.’ the officer said.

‘Car?’ Oscar asked angrily.

I swear to God if that fool is in my car with no fucking licence I’m gonna kill him Oscar thought.

But the car waiting for him wasn’t his and the teenager driving was his brother.

‘Hey there you free man!’ Ruby said awkwardly as he leaned against his crappy Subaru.

‘Why are you here?’ Oscar asked immediately.

‘Cesar had a class and he didn’t want you to have to walk all the way home so I’m your ride.’ Ruby said quickly.

Oscar nodded at him and tossed the boy his bag and watched the boy fumble it for a few seconds before he got a good hold on it.

‘Thanks.’ he said as he got in the passenger seat.

Ruby put his bag in the back seat and got in the car and put on his seat belt and checked his mirrors.

‘You got a licence fool?’

‘Yes. Got it last month and could you put on your seat belt? You know, click it or ticket.’ he said.

The Santo just looked at him.

‘Or I could just start driving, I’m sure you’re ready to go back home.’ Ruby squeaked as he started the car.

While they rode Oscar didn’t bother looking out the window, the hood was always the same. 

Ruby was a little different though.

He had gotten a few inches taller and his hair was styled different and a little longer than before, but over all he looked just as he had before.

‘Aye, how old are you now homie?’ he asked.

‘I’m eighteen, and that reminds me, I brought you little something. Look in the glove box.’

The cholo raised his brow and went for the glove box and found a tiny box wrapped in blue wrapping paper.

‘Open it.’ Ruby said eagerly.

Oscar unwrapped the gift a opened the box.

‘Cigarettes?’

‘Nah but Mario said you would appreciate a fake out, open the cigarettes.’

With a sigh Oscar opened the box and found a folded piece of paper and a key.

‘The fuck is this?’

‘The crime statistics, the crime rate has been at an all time low since the Profit$ got swept out. Yeah we still have like hella drug bust but other than a few small time muggings Freeridge is safer than its been in years.’ 

‘The key is for?’

‘Your restaurant.’

That made Oscar look over at the boy in the driver seat. 

‘My what?’

‘Your restaurant cholo, with the Profit$ gone and safe streets nearly all the Santos agreed to go legit for their money and decided since you “single handedly” brought in the clean Roller World money they would use a part of it to get you a legit place.’

The boy sat there with a big smile, looking all cute and and fucking legal while telling Oscar about safe streets and the restaurant he only let himself dream about.

‘Shut the fuck up homie, I do not like fucking lies.’ Oscar seethed as he threw the key and paper out the window.

‘Cesar said you’d do that, good thing I gave you the fake key.’ Ruby smiled as he pulled out a chain necklace that had a single key on it.

‘Stop fucking with me.’ the Santo warned.

‘If you really don’t believe me why don’t you see for yourself.’ the teenager challenged as he parked the car. 

For the first time Oscar looked out the window and saw that they were parked outside of a small building that had a big ass red SOLD sign on the glass door.

‘No.’ Oscar said as he got out of the car.

‘Are you gonna throw this?’ Ruby asked as he handed Oscar the key.

Without saying a word the cholo took the key and hurried out of the car, paying no mind to the boy complaining about filming the moment as he ran to the door.

He put in the key, and it fit.

‘No man.’ he said breathlessly as his eyes began to water.

‘Yes, now open the door and see your new place.’ Ruby smiled as he held up his phone.

Oscar held his breath as he turned the key and pushed the door open.

‘SURPRISE!!!’

There was his little brother, all his stupid little friends and all of his own closest boys and their hynas.

‘You fucking putas.’ he smiled as the tears fogged his vision.

‘Cry baby.’ Cesar teased as he pulled his big brother into a hug and gave his brother his first shot glass.

Oscar took the first drink as was Santo tradition for the guest of honor to have the first drink before the party begins.

The party itself is a blur of everyone congratulating him and thanking him for helping make the streets safer. In between that his brother gave him the details about the restaurant and what all he needed before he could legally open.

Right now it was just a few tables and chairs and people brought food and drinks from home, even still looking around and seeing the place he couldn’t believe it was his.

He was sitting at a table taking it all in when Cesar sat next to him.

‘You like it bro?’ he smiled.

‘Shut up...you know I love it. This is what I've wanted since before your little ass born.’ Oscar smiled.

‘Good, because Ruby near spazzed to death getting it ready for you. Granted I think he’s looking for a distraction right now.’ Cesar said before he took a sip of his beer.

‘Ruby planned this?’

‘Yeah, he talked a room full of Santos into giving you over half the Rollerworld money to start this up, and you know a party ain’t a party until Ruby micromanages it.’ his brother laughed.

‘And he did all that to distract from…’ Oscar asked, worried that maybe Ruby was still struggling after he got shot.

Cesar looked uncomfortable as his eyes landed on Mario who was dancing with his on and off girlfriend.

‘Him and Mario got beef right now, ever since Ruby came out Mari-’

‘Ruby’s gay?’ Oscar asked as he stood up.

‘Well he says the politically correct term is bisexual with a preference for women but-’

Oscar stopped listening and started scanning the room for Ruby.

‘Where is he?’

‘Why? Spook are gonna do something?’ his brother asked in worry.

‘No dumbass, at least nothing you want to hear about.’ he grinned.

‘Oh- Ah! Dude that’s so gross!’ Cesar complained as he realized why his brother was looking for one of his best friends.

‘You homophobic homie?’ Oscar asked.

‘No! Just the thought of my twenty five year old brother smashing my barely legal friend makes me wanna throw up my tamales.’

‘Where he at?’

‘He’s in the kitchen, and please if you do it use this.’ Cesar cringed as he handed his big brother a condom from his pocket.

‘Gracias.’ Oscar said as he walked through the small crowd and toward the kitchen door that was blocked by a red velvet rope.

He pushed it aside and walked in.

‘Staff only.’ Ruby said with his back turned to the door while he was writing on a clipboard.

‘I own the place.’

Ruby turned and sighed in relief when he saw Oscar.

‘Thank God, thought I’d have to wait until tomorrow, sign these.’ he said handing over the clipboard.

‘The deed, everything is paid for, you just need to sign and this place is legally in your name.’ Ruby smiled.

Oscar looked over the work and it was legit so he took a pen off Ruby’s shirt and signed where he needed.

‘Great I’ll file these in your office, because you have an office now and I already have a filing system. Its categorized by-’

‘I heard you’re gay.’

Ruby paused his story and seemed to bristle up like a angry little bird.

‘I’m bisexual with a prefre-’ this time Oscar interrupted him with a kiss.

Ruby’s eyes were wide and he was stiff as a statue, so Oscar pulled back.

‘First time you’ve done that chico?’

‘I-I-I ahem I’ve been kissed.’ Ruben stuttered.

‘Kissed any dudes before?’

‘Well not in reality but it has been a fantasy of mine for years.’

‘You ever had a man fuck you?’ Oscar asked as he took gentle the boy’s chin.

‘No…’ Ruby answered.

‘Do you want it?’ Oscar asked as he removed his shirt.

‘Oh wow, that is hot-I mean you look-’ the boy stuttered as he looked over Oscar’s muscled chest, he had definitely worked out in prison.

‘Chico...do you want me fuck you in that office?’ the cholo asked as he placed his hands on Ruby’s waist and gently pulled the boy closer to him.

Ruby looked baffled for a second before he took a deep breath.

‘No.’

Oscar was disappointed but he could respect a no.

‘I want you to fuck me here in your new kitchen.’ Ruby said before he grabbed Oscar’s face and pulled him down into a kiss.

The kiss was kinda clumsy and Ruby clearly didn’t have too much experience, but what he lacked in skill he made up for in enthusiasm.

While Oscar had kept his hands on the younger boy’s waist Ruby seemed to be trying to touch as much of the cholo as he could without breaking their kiss.

His hands were going over Oscar’s chest, up and down his arms and holding onto his face to keep him from pulling away.

If Ruby didn’t literally need oxygen to live then he never would have backed up to catch his breath.

Oscar watched in mild amusement as the boy take a few deep breaths.

‘Wow...didn’t think that would ever actually happen.’ Ruby said breathlessly.

‘You been thinking about kissing me chico?’ the cholo grinned making Ruby blush.

‘Well...how could I not? You pretty much forced me to have a crush on you, pinches cholo. Always showing up and helping me whenever I was losing my fucking mind, helping keep the Profit$ from hitting my house again. Then you came in like knight in shining armor to help Cesar, and that meant so much.’ the boy rambled.

‘Knight in Shining Armor? Me? A terrorizing gang banger?’ Oscar teased.

‘I was in the anger stage, and I didn’t like how fast you made my heart beat, I was still confused about guys and you weren’t exactly just some guy I thought was hot. You were-are one of the leaders of the Santos, and my best friend’s big brother.’ Ruby reasoned.

‘Well none of those things has changed, I’m still Cesar’s brother and I still lead the Santos.’

‘I’m not confused anymore.’ Ruby said before he tiptoed to kiss Oscar again.

This kiss was slower and less frantic and Oscar took control, actually getting in some tongue this time.

‘Mmm.’ the boy moaned into the kiss.

Oscar moved from Ruby’s lips to his jaw and down to his neck, placing small open mouth kisses there.

‘Oh my God Oscar.’ the boy moaned as he held onto the man kissing his neck.

‘I ain’t started yet baby.’ the older man growled into Ruby’s ear before he bit down in his earlobe making him gasp in shock.

Oscar effortlessly picked up the teenager, Ruby was just as light as he thought he would be.

The surprise of suddenly being lifted made the boy very aware of what’s happening right now.

‘Wait, hold on!’ he said quickly.

Immediately Oscar let go of him and watched in confusion as Ruben frantically searched his pockets, and as he was very surprised and amused to see Ruby pull out a condom and a small tube of lube.

He couldn’t help himself, he didn’t mean to but Oscar started laughing.

‘Don’t laugh, I have been planning on losing my virginity since I was fifteen. I’m always ready in case a telenovela moment pops up, which sounds dumb but is actually really smart. And since I’m into dudes now and I’m pretty sure I’m a bottom I started you know...cleaning it.’

Oscar was in stitches he hadn’t laughed this hard since he got locked up, not even Cesar made him laugh like this.

He calmed himself and apologized with a kiss on Ruby's temple.

‘Not gonna lie, I haven’t had a virgin in a while, but don’t worry. I’ll be very gentle chico.’ Oscar whispered quietly before he pulled the boy back into a kiss.

Nice and slowly he pushed Ruby back until he was against a prep table and gently lifted him up and placed him on it.

Almost instinctively the boy spread his legs enough for Oscar to settle in between them.

Their kisses have been officially upgraded to full on making out, making out with intent.  
Oscar started unbuttoning Ruby’s shirt.

‘Oh wow we are really doing this.’ the boy sighed as the shirt was removed.

‘Tell me if you wanna stop, because if you do then I will back up.’ Oscar assured as he looked at the bullet wound.

‘Please don’t stop now Spook...I waited too long for this’ Ruby whined before he placed a nervous kiss on the gang leader’s neck tat.

Oscar smiled at the boy in his arms.

‘I never told you how much I like hearing you call me Spooky.’

‘I’ll call you Spooky as much as you want, just please take the rest of our clothes off and have sex with me.’ 

Again the cholo couldn’t help but chuckle as he pushed the boy back on the table and undid his belt buckle.

‘Got that ass nice and squeaky clean for me baby?’ Oscar asked as he pulled down Ruby’s pants and boxers, even removing the socks and shoes at the same time.

He looked at the boy’s naked body, taking in the tan skin and the few moles here and there and even that bullet wound he blamed himself for. Then his eyes went lower and he looked at Ruby’s erection, it was only about six inches but it was rock hard and literally twitching.

‘Excited for me?’

‘Yes, please use the lube.’ Ruby begged as he offered up the tube.

Oscar took it put a little on his hand and rubbing them together before he took hold of Ruby’s cock and started stroking it nice and slow.

‘Oh fuck.’ Ruby moaned as his head fell back in pleasure, no one other than him had ever touched his dick before and honestly felt a million times better when it was someone else’s hand 

The Santo kept stroking nice and slow as he used his other hand to slowly start massaging the ring of Ruby’s asshole.

Ruby gasped at this and tensed up.

‘Shhh...relax chico, let Spooky take care of you. Nice and slow baby...nice and slow.’ Oscar soothed, still keeping his strokes slow and steady.

It took Ruby a second to relax again and when he did Oscar put a little more pressure on his hole and pushed his finger in, only the first knuckle deep.

‘Woah, woah, OK. that is your finger in my ass isn’t it?’

‘Yes.’ Oscar said as he pushed his finger in completely.

‘Ooooh OK, fuck, that is a full finger.’

‘Yes...how does it feel?’ 

‘Uh...weird as hell, doesn’t hurt it’s just...that hole is usually exit only, and it feels weird having something just sitting there. Try moving it a little.’ Ruby answered.

Oscar nodded and started moving his thrusting his finger in and out, all the while he never stopped stroking Ruby’s dick.

‘Oh yeah, that is...that is way better oh fuck.’ the younger man moaned.

The cholo kept his pace nice and slow.

‘I’m about to put in another.’ Oscar warned.

’Do you have to?’ Ruby asked.

‘My dick is bigger than my finger chico, you need to be stretched.’

He added a little more lube to his fingers and started pushing in his second finger.

‘Ow ow OK, that one does hurt.’ Ruby complained. 

‘I know chico, just keep breathing, nice and slow deep breaths.’ Oscar comforted.

The cholo was gentle and patient, nothing at all like what Ruby thought he would be like when he used to beat his meat when he was sixteen. He thought his first time with Oscar would be hard, rough...and totally hot, but slow and caring was even better.

‘Kiss me.’ Oscar said.

Ruby looked up at the man standing above him and sat up to kiss him, this one wasn’t slow and sweet or fast and heated; it was passionate.

‘Undo my pants.’ Oscar said.

‘Yes...Spooky.’ Ruby smiled as he slowly undid his the older man’s khaki pants.

‘Never thought I’d ever get to actually do this, never thought I’d see it unless I walked in on you peeing and then you’d kill me.’ he rambled before he pushed down Oscar’s pants and boxers.

‘Holy shit!’ the younger one gasped.

‘I know.’ Oscar grinned.

‘You asshole, there was no way that your fingers were going to prepare me for this. It’s...fucking huge.’ Ruby said in completely awe.

‘Thank you, I grew it myself.’ Oscar teased.

‘Can I touch it.’

‘Kind of necessary.’ 

Ruby pouted at Oscar’s teasing and the cholo smiled as he took Ruby’s wrist and slid the other guys hand into his pants.

‘Oh my god it-’ Ruby started but was interrupted by Oscar changing the position of his fingers that were still in his ass.

They were hitting a spot that he had done plenty of research on but had been too scared to explore it himself.

‘Ah...Spooky.’ 

‘Found your spot chico.’

Oscar started to move his fingers faster and picking up speed on stroking Ruby’s cock, honestly it felt good...like really really good.

Too fucking good.

Ruby had tried not to moan and whimper, but he couldn’t help it. Every time Oscar curved his fingers and hit that spot he found himself whining in pleasure. 

‘Oh f-fuck, Spook I’m-I’m getting close! Fuck I’m gonna cum, you’re gonna make me cum Spooky!’ Ruby moaned as he clung to Oscar’s shoulders as he struggled to hold back his orgasm.

‘Cum for me chico.’ Oscar growled as he rapidly slamming his fingers into Ruby’s prostate.

Ruby dug his fingernails into Oscar’s shoulders and buried his face in Oscar’s neck.

‘Oh fuck!’ he cried out as he came harder than he ever has in his entire life, all the while Oscar kept stroking and fingering him. 

Ruby had to physically take hold of Oscar’s wrists to stop him so that he could catch his breath and come down from his high.

‘Oh my God that was intense.’ the boy pants as he looks down at the mess he’s left on his stomach.

‘We ain't done here chico.’ Oscar said as he held up the condom.

‘Fuck.’ Ruby sighed as he laid back.

‘Relax chico.’

‘OK, just go slow. Very slow.’

Oscar put on the condom and added some more lube to both himself and Ruby.

‘Ready?’ he asked.

‘Yeah.’ Ruby said nervously.

With a sigh Oscar pushed in slowly, thinking about how long he’s wanted this and how he doesn’t want to fuck it up by getting carried away and hurting Ruby.

Even though this was the tightest hole he’s ever been in and all he wanted was to fuck into as hard as he could.

Ruby winced and whined as Oscar entered him slowly, once he had bottomed out he sat still and let Ruby adjust to his size.

It took him a while but eventually Ruby relaxed.

‘OK, you can move now.’

‘You sure chico?’

‘Please Spooky.’ he begged, looking up at the cholo with pleading eyes.

Oscar couldn’t say no to that face, especially not while he was already inside of the tight ass he had been looking at for so long.

He pulled out a bit and very slowly pushed back into him, watching Ruby’s face to make sure he wasn’t hurting. He found Ruby’s face wasn’t scrunched in pain, but rather his eyes were closed and mouth hung open in a silent cry of pleasure.

Taking that as a good sign Oscar set a slow pace, really enjoying the feeling of being in Ruby’s tight hole.

Oscar was not the only one enjoying it, the feeling had originally hurt like hell, like he was being split in two. Then the pain eased into pleasure and just looking up at Oscar above him...nothing would ever be better than this.

‘Faster…’ he moaned.

The cholo had no issue following that order, tightening his grip on Ruby’s waist before he added a bit more speed and force to his thrusts.

‘Oh fuck.’ Oscar grunted in pleasure.

Soon the kitchen was filled with Oscar’s grunts and Ruby’s whines, cries and moans, if it hadn’t been for the music playing in the dining area and that stupid rope then everyone would know exactly what was going on.

Then faster than he had wished Oscar felt his balls start to tighten and the heat pool in his stomach, he was getting close, but he wanted to see to it that Ruby came before him.

He kept his thrusts hard and fast as he took hold of Ruby’s cock once again.

‘Oh my god Spooky!’ Ruby cried out.

‘Cum for me baby.’

‘It’s too much...I already-’

‘I said cum for your Papi.’ Oscar growled as his thrusts became erratic.

Ruby’s vision went white as he came so hard he thought he was gonna turn inside out, he couldn’t even register that the inhumane whining noise was coming from his own mouth. 

Oscar couldn’t hold out another second, not when Ruby’s ass was tightening up around his cock like this.

‘Fuck!’ he grunted as he unleashed his own load.

With a great sigh he collapsed on top of Ruby and together they tried to catch their breath.

‘That was amazing.’

‘Yeah.’ Oscar panted.

‘Were you into dudes the whole time?’ Ruby asked.

‘I’m into nice asses, and you have the best one I’ve seen in this shit town.’ 

‘Thanks, but was that all this was, you find out I’m legal and mildly into guys and decide to take my superb ass? Then after we just move on...nail and bail like I'm some pass around hyna?’ Ruby asked as he pushed Oscar off him a bit.

Instead of an answer Ruby received a small slap on the forehead.

'Dumbass, I waited too long and thought about you too much to just nail and bail. Besides I'm gonna need a partner with some business knowledge to help me get this place running.’

'You thought about me?’

'Everyday since the summer before Cesar got jumped in.’ 

‘And now that you've had me...and you clearly liked me are we like together now?’ Ruby asked.

‘Yes chico.’

A smile brighter than the sun took over Ruby's face as he pulled Oscar down into a kiss.

Before Ruby could deepen the kiss Oscar was picking him up and carrying him toward the small office.

'Where are we going?’ he asked.

'I'm gonna fuck you in my new office.’ Oscar answered.

'But we just-’ 

'I know.'


End file.
